Scot Chisholm & Co. 

Every week I tackle management, operations & startup topics that are helping 100,000+ people become better leaders.

Scot’s Newsletter

Highland

Highland is a “school” & community for founders. If you're a founder/CEO, we should talk!

Founder & Chief Professor

Tall Timbers Holding Co.

A family office and holding company with wholly owned businesses, private investments, and property holdings.

Managing Director & Founder

GoFundMe

After the merger of Classy and GoFundMe, I’ve taken on a strategic advisory role to the CEO & executive team, mainly focused on longer-range product strategy and M&A

Strategic Advisor, GoFundMe & Classy

Classy

Founder & Strategic Advisor (Acq. by GoFundMe, 2022)

Founder & Chairman

Classy is a SaaS giving platform that powers the fundraising of over 10,000 nonprofit organizations. Classy is a certified B-Corp, has a team of 300+ people and has raised over $5 billion for social good since 2011.

CEO & Founder

In Classy’s earliest days, we hosted large scale fundraising events with the goal of connecting millennials with local nonprofits in the San Diego area.

CEO & Founder (pre tech company)

Haskill Creek

Haskill Creek is a new type of self-care store. Imagine a healthier & more holistic version of a Walgreens or CVS. Family owned business.

Co-Founder

ALBION SC

Albion Soccer Club is one of the top youth soccer franchises in the United States with over 10,000 players and hundreds of teams across the country.

Co-Owner

Save Farmland

Save Farmland is a nonprofit organization with a mission to protect and promote small farms in Flathead Valley, Montana, and beyond.

Abundant Montana

Board Member

AERO Montana

Abundant Montana (a program of Aero), makes it easy for anyone to find and choose local food in Montana.

Advisory Board

CEO, Highland & Haskill Creek • Founder of Classy (acq. by GoFundMe) • Founder of nonprofit, Save Farmland

Multi-time founder but operator at heart. 

Industrial engineer and lean six sigma nerd by training. 

Now I write about management, operations & startup topics that are helping 200,000+ people become better leaders.

scotchisholm.com/newsletter


MY BACKGROUND ————— 

🚀 Founder of Classy, a SaaS platform for 10k+ nonprofits raising billions per year. 

🎗️Acquired by GoFundMe in ‘22 to create the largest giving platform in the world. Together we’ve raised over $30 billion for individual & nonprofit causes. 

🏔️ Founder of Highland, a private community & leadership “school” for high-potential founders. 

🏡 Co-founder of Haskill Creek, a much healthier version of a Walgreens or CVS. 

🧑🏼‍🌾 Founder of Save Farmland, a nonprofit protecting local farmland. 

⚽️ Co-owner of Albion Soccer Club, top youth soccer club in country

❤️ Board experience: Nature Conservancy, Abundant Montana, Team Rubicon, Street Soccer USA, Montana Pediatric Cancer Foundation 


👇 WAYS TO CONNECT —————

→ Podcast / speaking oppty? email: partner@scotchisholm.com

→ Join my free newsletter: https://scotchisholm.com/newsletter-linkedin-profile

→ Check out my private community for founders: www.joinhighland.com

Scot Chisholm

Sh*tty managers ruin lives. 
Great managers change them. 

I’ve managed hundreds of people over the last 20 years. 

One of my biggest takeaways is the massive difference between an average manager and a truly great one. 

But, here’s the truth:

No one starts out as a great manager (literally no one). 

And, becoming a great manager can be learned by anyone. 

Just focus on these 12 habits:

1/ Provide business context
2/ Set high standards
3/ Take full ownership
4/ Focus (then focus again)
5/ Create operating cohesion 
6/ Lead with data
7/ But be decisive 
8/ Let your team make decisions
9/ Don’t give sh*tty feedback
10/ Take feedback like an adult
11/ Listen more than you talk
12/ Always be learning

The gap in quality managers is large, but the right behaviors are simple. 

Focus on these 12 habits daily and you’ll be ahead of 99%. 

What habits resonated most?
Let me know in the comments 👇

⁂

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Operator & Investor • Founder of Classy (acq. by GoFundMe) • Building Highland, Just, Haskill Creek

12 insanely simple habits to become a high performing mana

Leadership is misunderstood.

Building Classy taught me that the best leaders aren't necessarily the ones with the biggest titles, or the ones who can charm a room.

Some of the best leaders in our 300+ person company were individual contributors at the very bottom of the org chart. Young managers. First-time team leads.

Over the years I started noticing what made these unlikely leaders so effective. They had traits that, quite honestly, my executives lacked at times. Including me.

Over time I boiled them down to 10 core traits that our best leaders always exhibited. It’s no surprise they rose fast within the company. Many are still there today, 15 years later.  

The very best leaders: 

• Clarify - Never assume everyone understands
• Believe - Push forward when everyone doubts
• Adapt - Evolve rapidly without ego
• Anticipate - Solve problems before they explode
• Persist - Get kicked in the teeth, get up anyway
• Empower - Create leaders, not followers
• Own - Own failures without excuses
• Hold the line - When quality dips and others compromise
• Always Learn - Learn and grow faster than the company
• Lead by Example - Live values when no one's watching

Most leaders start off strong in a few, but not all of these traits. You must intentionally develop them over time. It's a lifelong thing. 

But many executives forget this. Maybe they were great once. But they start slipping. They stop learning. They get cocky. I've seen this too many times. 

I don't care where you’re at in your career. Keep these traits in mind. And never stop developing them. 

⁂

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Top 10 traits of the very best leaders:

Every high performance culture starts with this… 

I recently asked a founder about his culture. And he started talking about free lunches and other perks. 

This is not culture. 

He was a coaching client of mine, so I nicely explained… 

Here's what real culture looks like: 
→ A shared purpose. Everyone understands and resonates with the 'Why'.

→ Excitement about the future. The vision is clear to all and it creates an almost kid-like excitement about the future.

→ Strong empathy and trust. Great orgs know if you neglect empathy, trust evaporates.

→ The correct level of accountability. People know you're building a championship team.

→ Mutual respect and encouragement. High performers have admiration for each other.

→ Hunger to learn and improve. Without being asked. That's the diet of champions.

→ Aligned financial incentives. Compensation that's aligned to the organization's top goals.

→ Career mobility. Lots of opportunity, with clear expectations around advancement.

→ Work-life balance. Clear boundaries that are enforced across the org.

→ Pride in the work. Numbers one through nine create an amazing sense of pride. You'll find yourself bragging about work to complete strangers.


When you get the culture right, people are excited to show up, employees self-manage, and retention is extremely high. 

And great business results naturally follow.

 ⁂

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10 signs of great culture.

Most people waste their leadership meetings. 

Do this instead: 

When I was building Classy I got this meeting wrong for years. We’d talk about everything BUT the important stuff. Too much time wasted on low-level “issues”. Too many tangents and distractions. Everyone left feeling:

• Confused
• Misaligned 
• Unaccountable

I talked to advisors and scoured the internet for help. But it took loads of trial and error to land on a meeting structure that actually worked. We stuck with it for nearly ten years. 

One of the major improvements was focus. Teams spend months setting goals only to let them collect dust. Your leadership meeting should be your #1 checkpoint for progress. 

Once we got “tight at the top” as a leadership team, everything started to change. More results, less talk. It became the tip of the spear of our entire operating rhythm.

To this day, I call it your most important meeting. If I only had one, it’d be the leadership meeting. 

The entire leadership team meeting structure is in the carousel. Copy it for your own company and let me know what you think. 

⁂

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How to nail your  leadership meeting every time:

Most people think goals fail because the team screwed up. 

They’re wrong. 

99% of goals fail because of poor leadership.

It doesn’t matter what framework you use…

→ OKRs
→ Rocks
→ SMART

If you’re sloppy with your approach, the company won’t hit its goals. 

That’s on you. 

I learned this the hard way, running a company with hundreds of people. 

Now I see it working with nearly 100 CEOs across all industries. 

Here are 7 non-negotiable rules that will make your goal-setting 10x better…

(regardless of your framework) 

⁂

Rule 1 –  
Focus (then focus again):

• Maximum three goals, period
• Goals aren't task lists
• Everything priority = nothing priority

Rule 2 – 
Always be measurable: 

• Three metrics maximum per goal
• Measure outcomes, not tasks
• "$1M ARR" beats "update deck"

Rule 3 – 
Challenging but realistic: 

• Impossible goals kill momentum
• Stretch without delusion
• No sandbagging, mutual accountability

Rule 4 – 
Never forget the ‘why’: 

• No context leaves team guessing
• Each goal deserves a 'why'
• 1-3 sentence rationale

Rule 5 – 
Track consistently:

• Break annual into monthly
• Weekly red/yellow/green updates
• Never leave dashboards stale

Rule 6 – 
Create accountability:

• Use leadership meeting
• Address every yellow or red
• 20% status, 80% solving

Rule 7 – 
Align incentives:

• Pay goals to comp
• Ignore the OKR purists
• Bonus plan is perfect for this

Does this resonate? 
What rules would you add?
Let me know in the comments 👇

 ⁂

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How to actually achieve your company goals in 2026

If there's one thing you do on Linkedin today... 

I'd be forever grateful if you'd consider applying, or sharing this role with someone you really respect. 

Christopher Himes & I started dreaming up this company about a year ago.  Now the dream has turned to reality. 

With a fresh round, a tiny team of insane talent, and a massive opportunity in front of us... 

We. are. ready. to. go!

Who wants to join us? 

p.s. We're not listing this company as "stealth" because that's dumb. But you'll learn way more about the market, opportunity and product when you apply. Trust me its badass. 

🔥

Dream Weavers Foundation

Founder & President

Lush Decor Home

Founder & Co-Chair of the Board

Founder & CEO

Entrepreneur #LushDecor | Finding Strength and Purpose in Life’s Twists and Turns | Living an Inspired Life | YPO, WPO #DreamWeaverbook & shortfilm #LifeInspired #Author #DefyOdds #OvercomeChallenges #PersonalGrowth

Would you believe that a girl from a remote village in Shandong, China, without electricity or basic amenities, could one day stand as a Chairwoman of the Board on the global stage? This is my story—my journey from humble beginnings to the forefront of entrepreneurship and empowerment.

My early years were filled with determination to change my family's fate. From working as a hotel maid, an esthetician, to running a dry cleaning business and even starting a matchmaking service for successful women, each step was a leap towards a bigger dream. The adventure took a daring turn when I moved to the United States in my mid-20s, with little English, starting as a nanny before diving into design studies.

The real test came in 2008, during the financial crisis. With a one-year-old baby by my side and on the brink of single motherhood, I founded Lush Décor Home. My path was not easy, strewn with business betrayals, two amicable divorces, and a leap into the unknown world of private equity for my first business exit. Despite initially not knowing what "PE" stood for, I navigated my way to financial freedom and handed over the torch to a talented leadership team, led by a woman CEO Paola Pretti, as I embraced the role of Chairwoman of the Board and Chief Purpose Officer.

This journey has been about more than just overcoming challenges; it's been a process of continuous learning and standing up after countless failures. Today, I am a dedicated champion for girls and women everywhere. Through sharing my story, I aim to instill hope and strength in those who find themselves in the shoes of my younger self or facing similar battles.

So, if you asked me years ago if I believed that girl from the village could achieve all this, my answer would have been fueled by hope, but shrouded in doubt. Yet, here I am. This narrative is a living proof that with unwavering determination, the support of professional communities, and the courage to take risks, breaking barriers and achieving dreams isn't just possible—it's inevitable.

To everyone facing their own set of challenges, remember: Your beginning does not define your destiny. With each step forward, you too can transform your dreams from mere fantasies into your reality. Let's embark on this journey of empowerment together, breaking barriers and redefining what's possible. 

Join me for shared experience and find me on Instagram too @jennyjingzhu

Jenny (Jing) Zhu

The Power Suit & The Power of Sisterhood.

Some clothes make you feel unstoppable. When I put on a piece from my dear friend Deirdre Quinn’s brand, Lafayette 148 New York, I feel like I can tackle any turnaround, any challenge.

This look isn't just fabric; it’s a tangible thread of confidence and resilience. I stand taller knowing it was created by a fellow woman entrepreneur who understands that strength and style go hand-in-hand.

To every woman building, leading, and juggling—remember that sisterhood is the strongest thread in our tapestry. When we support each other’s vision, we all rise higher.

Cheers to the women weaving success together! 

What's the best piece of business advice you've received from a female friend? Share it below! 👇

#Lafayette148 #DeirdreQuinn #FemaleFounders #WomenWhoRise #Sisterhood #DreamWeaver #PowerSuit #ConfidenceIsKey #StilettoStrapping Women Presidents Organization C200 Women Elevating Women™

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Some of the most meaningful moments after a speech or panel happen during the book signing. 

It is in that space where the conversation becomes human and personal. Every handshake, every story, and every reflection reminds me why I wrote Dream Weaver and why sharing our stories matters.

When I hear about your journeys, your obstacles, the chapters you are proud of, and even the ones that broke you open, I feel the thread that connects us all. These moments remind me that leadership, entrepreneurship, and reinvention are never solitary experiences. 

We learn from one another. 

We rise through one another. 

We grow because of one another.

Thank you to everyone who has shared a piece of your life with me and allowed my story to touch yours. I carry these exchanges with me. They inspire how I show up, write, and lead. 

#DreamWeaverBook #LeadershipJourney #WomenWhoInspire #DreamWeaverCommunity #AuthorLife

There is a special kind of energy that rises when people come together with a shared belief in amplifying women’s voices and stories.

That spirit filled the room at the Dream Weaver NYC Premiere. It was powerful to stand on that stage knowing that every person in the audience was there because they believe in the importance of storytelling, representation, and lifting voices that are too often overlooked.

I want to extend my heartfelt gratitude to the partners who helped make this event possible. Thank you to The Wires, Lush Decor, Q Qingqing Lan ‘s Mandarin, Crimson Strategy Group, Bill Kwon , and Indigo River Publishing. 

Your support reflects a meaningful commitment to creating space for women to be heard, seen, and celebrated. Your belief in this mission helped bring this premiere to life.

Looking out into that room reminded me why I started this journey. It showed me how much impact is possible when communities come together with intention and purpose. Thank you to everyone who joined us and helped create a night filled with connection, encouragement, and hope.

You lifted this dream with me.

#DreamWeaverNYC #DreamWeaverFilm #DreamWeavers #WomenWhoLead #PartnerInPurpose #AmplifyingVoices

The Hard Truth: My Lessons on Betrayal, Burnout, and Climbing Back Up
 
I had the privilege of joining a conversation that got raw and real—the way I prefer all my business talks. Thank you to PNC  for inviting me to an event that truly was more than a panel; it was group therapy for entrepreneurs.

When authentic leaders dare to talk about the business betrayal, the crippling burnout, and the financial rock bottoms that nearly break us, that’s when we truly give permission to others to begin healing and growing. We stop pretending the road is linear.

I was honored to share the stage and strengthen my own tapestry alongside:
-Kiya Tomlin  and Vanessa Deleon: Two incredible founders whose creativity and fierce determination should be required reading for every aspiring entrepreneur.

-Louis Cestello, Anusha Gibson , Hyejin Oh, and Aimee Sheenan: Leaders who consistently demonstrate that power is best wielded with heart and empowerment. Your support makes this work possible.

-Shana Peterson Sheptak: For asking the tough questions and navigating the messy twists and turns that define a founder's life.

4 Threads I Shared From My Journey:

1️⃣ The "Jinglish" Years: How I navigated the 2008 crisis and built Lush Decor as a young immigrant and new mother, relying on raw grit and broken English. I proved that passion overcomes the language barrier.

2️⃣ The Cost of Naiveté: The non-negotiable lessons learned after a business partner's betrayal forced me to fight for my company, ultimately teaching me how to survive as a leader, mother, and ex-wife—all at once.

3️⃣ Capital is Confidence: Why finding access to capital is a deep reflection of self-trust, and why chasing money without mission is a recipe for emptiness.

4️⃣ Embrace the Flaws: Your struggles aren't setbacks; they are the unique colors and textures in your tapestry. Don't hide them—they are your strength.

Events like this remind me why I keep going. When we choose vulnerability and growth over perfection, we strengthen the entire community. Thank you to everyone who showed up ready to be seen.

Let’s keep weaving! What is the hardest thread you’ve had to weave into your business? Share it below. 👇

#PNC #WomenInLeadership #DreamWeaver #AuthenticLeadership #ImmigrantFounder #BusinessBetrayal #StilettoStrapping #LeadershipWithPurpose

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The Battle

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